Downtown Stamford Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Downtown Stamford

Price found within the past 48 hours. Click for updated prices.
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Price was CA $1,725, price is now CA $981 per person
CA $981
per person
May 16 - May 20
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
2/10 (2 reviews)
Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

2 out of 5
Bryn Mawr
Price was CA $3,332, price is now CA $1,983 per person
CA $1,983
per person
Jun 6 - Jun 8
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.

Reviewed on Feb 27, 2026

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

4 out of 5
Price was CA $3,391, price is now CA $2,191 per person
CA $2,191
per person
Jun 6 - Jun 8
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
No reviews
Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking

2 out of 5
Price was CA $3,391, price is now CA $2,191 per person
CA $2,191
per person
Jun 6 - Jun 8
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
No reviews
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

2 out of 5
Southeast Yonkers
Price was CA $3,332, price is now CA $2,155 per person
CA $2,155
per person
Jun 6 - Jun 8
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very Good! (1 review)

Where to stay in Downtown Stamford

Find the best Downtown Stamford areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Stamford
Stamford City Harbor Point Landscape with tall office buildings, park benches, boardwalk footpaths, and moored boats at the dock on a dramatic stormy winter in Connecticut

Cove - East Side - Shippan

3 out of top 10 points of interest in this area

While visiting Cove - East Side - Shippan, you might make a stop by sights like West Beach and Chelsea Piers.

Find hotels in Cove - East Side - Shippan

Downtown Stamford Hotel Deals

Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Apr 15 to Apr 16
CA $137
CA $158 total
Apr 15 - Apr 16
includes taxes & fees
8.4/10 Very Good! (1,745 reviews)
Safe, no frills, a bit on the gritty side but you get what you pay for.Friendly staff, decent contentail breakfast, secure convenient parking. The rooms are dated and could be cleaner. Stains on the carpet, visible biofilm in the sink, sealing tiles in bathroom sagging and stained from water damage. ...

Reviewed on Apr 12, 2026

Amsterdam Hotel
The Stamford Hotel

The Stamford Hotel

3.5 out of 5
700 East Main Street Stamford CT
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Apr 20 to Apr 21
CA $210
CA $241 total
Apr 20 - Apr 21
includes taxes & fees
7.8/10 Good! (1,153 reviews)
Old hotel. For example carpet in the corridor has bumps. The first day the shower was tepid but the problem was fixed on the second day. The toilet paper is the super thin kind that you need to fold 20 times and still falls apart. There is no espresso machine in lobby and I consider that a minimum ...

Reviewed on Apr 10, 2026

The Stamford Hotel
Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa

3.5 out of 5
243 Tresser Blvd Stamford CT
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Apr 30 to May 1
CA $268
CA $309 total
Apr 30 - May 1
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Toilet and shower wasn’t working.

Reviewed on Apr 2, 2026

Stamford Marriott Hotel & Spa
See all 1,183 properties in Downtown Stamford
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Downtown Stamford vacation package cost?
Starting from as little as CA $981, you can handcraft your own Downtown Stamford vacation package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Downtown Stamford?
You'll save loads of cash if you bundle your hotels, car rentals and flights into a Downtown Stamford travel package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 airlines and 1,000,000 hotels globally, so you'll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Downtown Stamford?
With lots to discover in Downtown Stamford, it's a good idea to stay near its attractions. Chelsea Piers, Stamford Town Center and Cove Island Park are some top ones to add to your must-see list.
What are the top hotels in Downtown Stamford?
Apartments At Greyrock and Residence Inn Stamford Downtown are among the most popular hotels in Downtown Stamford. Why not check out the rates and amenities at each and then decide?
How far in advance should I book my Downtown Stamford vacation?
Travelers are generally able to browse international flights on Expedia up to a year in advance of departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Downtown Stamford travel package include?
Expedia has all you need to book your Downtown Stamford escape, but what goes into your package is totally up to you. Select from a combination of rental cars, flights and hotels. Chasing some tours or activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your budget, there's a deal to match your needs.
What should I know before booking a Downtown Stamford travel package?
You can look forward to saving with an Expedia travel package. Bundle your airfares, rental cars and hotels and land terrific discounts. You're not restricted to hotels, however. Book with us and take your pick of beachside condos, cabins in the mountains and even houseboats and castles!
Can I choose my airline with a Downtown Stamford Expedia vacation package?
Yes — that's the beauty of an Expedia package. You can pick and choose your flights, hotels and more. We have more than 550 partner airlines around the world, so you have loads of choice when organizing your Downtown Stamford trip.
If I'm not able to travel, can I cancel my Downtown Stamford vacation package?
You can. We get that things don't always go to plan, so we're happy to help if you need to make changes to your Downtown Stamford vacation package. You may be able to cancel or change your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Look up our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Downtown Stamford

Museum of Black World War II History

You can study the exhibits at Museum of Black World War II History, a museum with a storied past, during your travels to Stamford. Check out the shops and top-notch restaurants in this romantic area.

Museum of Black World War II History

Things to do

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $1,705
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Stamford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.